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Larry Kalkstein used to be a millionaire. At least, that’s what he tells me. It’s a spring night and I’m running late as I head from Manhattan’s Upper East Side to the trendier Downtown neighbourhood of Chelsea, so I catch a cab. Larry, my driver, a raspy-voiced man in his 70s, starts talking.

He had a $15m art collection, he says; an apartment on the upscale Upper West Side. That was before the prostate cancer, the bad investments.

“You don’t believe me?”

Before I can stop him, he drives me to a magnificent beaux-arts building on West 79th Street. He rolls up his window, greets the doorman.

“Manuel! How are you doing? Retired yet?”

The doorman, recognising Larry, smiles and greets him back.

That, Larry says, is what happens in New York. One minute you’re on top, the next minute you’ve got nothing. It’s not so bad, though. One of his cousins, a millionaire — “a small millionaire, not like Donald Trump” — has a building on the Upper East Side, and lets him live in a little apartment there. He walks his dog in Carl Schurz Park, overlooking the East River. He gets by.

Larry takes me on a detour through the Upper West Side, where — with salty intensity — he decries everything that’s happened to New York in the past 20 years. “The neighbourhoods have changed,” he sighs: “everything’s gotten more expensive, chain stores everywhere, Uber drivers undercutting old-fashioned cab drivers. Everything changes so quickly; everyone just cares about making money.” A pause. “I can’t be like these jerks,” he adds (the noun he actually uses is stronger). He’s driven women in labour to the hospital, he says, and never once charged them.

Larry starts to reminisce about the artistic luminaries he’s met and known — he had an uncle who was close to Noël Coward, he says; he’s met Keith Richards and Elizabeth Taylor in their heydays. Larry pulls out a newspaper clipping from 1951 — a record of Albert Einstein’s visit to America. He was just a boy at the time, he says, but managed to meet the physicist through an uncle who played in the Israeli Philharmonic. Back then, after all, New York was a place where anything could happen.

“Of course, New York’s not what it used to be.”

If any one thing characterises this iconic city, it’s the constancy of its change. Wildly expensive — and getting pricier all the time — with a dynamic, if frenetic, trend-based culture that means the next in-thing is already on its way out by the time anybody hears about it, New York always feels like a place for the young (or, at least, the young and well-heeled). Neighbourhoods change overnight — quiet middle-class enclaves or run-down warehouse districts turn into hipster joints; hipster joints become overrun, in turn, by double-wide buggies and organic food chains.

I’ve seen more New Yorks than most. I grew up on the Upper East Side, a largely residential district of Manhattan known for its proximity to museums and Central Park and its staid, even stuffy, character. I spent my teenage years in the East Village, trying on pink wigs at Ricky’s (other cities have the pharmacy Duane Reade; we have a drugstore chain that got its start selling sex toys and makeup to drag queens), drinking coffee and eating late-night pierogi at 24/7 Ukranian restaurants like the iconic Veselka, and going cross-town for a midnight interactive screening of The Rocky Horror Picture Show in Chelsea.

But, heading back for Easter in preparation for a permanent return after almost a decade away, I find that I look at the city with fresh eyes. Neighbourhoods that were barely burgeoning when I left — Williamsburg, say — are now more expensive than Manhattan; places that weren’t even on the map when I left — Crown Heights, for example — seem today to have more European tourists than locals.

Some places, though, have stayed the same. Not long after my return, I head to Doyers Street, in Chinatown. One of the few ethnic enclaves in pricey Lower Manhattan to resist the city’s constant waves of gentrification, Chinatown — with its warren of restaurants and herb shops, tea salons and outdoor stalls selling hats or scarves or jackfruit from Malaysia — is also among Manhattan’s most historic. Doyers Street, an L-shaped pedestrianised alley between two larger thoroughfares, was once known as the ‘Bloody Angle’: the most dangerous street in New York City. Back in the late 19th century, the area was famous for its opium dens, brothels, and gambling houses catering to single men (most of the Chinese immigrants of the time were men brought over to work on railroads, making for a wildly uneven gender ratio), as well as for the gangs that oversaw the rackets. During this period, and for the first decades of the 20th century, Doyers Street was the city’s most infamous spot for gang warfare and murder — its blind corners making illicit activity that much harder to spot.

Nom Wah Tea Parlor, at number 13, dates back to this era. Founded in 1920, the restaurant still has plenty of its antique fixings: from an art deco cash register to its mid-century bar stools (its prices, too, are a throwback, by NYC standards: main courses can be had for as little as $5). Over a dinner of fried chicken feet (chewy) and lightly steamed chive buns (far more digestible), I watch the clientele: although there are a few tourists here, along with the odd hipster, most of the customers are Chinese, and seem to be local.

Next door, however, it’s a different story. Behind the unmarked doors at 9 Doyers Street lies Apotheke: one of the city’s many unmarked, 1920s-style speakeasy bars, which require ingenuity or a hook-up (or a knack for Google) to enter. Some, like Garfunkel’s on Clinton Street, can only be accessed via an ‘employees only’ door in another bar. Others, like PDT (Please Don’t Tell), on St Marks Place, have you enter through a phone booth. Apotheke only requires a password, which you get when you make a reservation. The low-lit, Gatsby-inspired zinc bar holds ingredients for mixologist Albert Trummer’s 20 or so cocktails: each sounding less like a drink and more like modern art.

Many of the ingredients on offer are a nod to the neighbourhood’s history as a hub for Traditional Chinese Medicine. They include deer velvet, which, according to a po-faced waitress, is the fuzz one scrapes off deer antlers. Apparently it’s an aphrodisiac. I order the Siren’s Call, a nautical-themed drink containing gin, roasted seaweed, ginger cucumber and salt. Dyed black with squid ink, it arrives with a garnish: a mussel shell containing a single chocolate pearl.

To its credit, it tasted exactly like the bottom of the sea. I didn’t finish it. At $25, it cost more than my dinner, with wine, next door. Yet I leave Apotheke feeling happy, even buoyant. As I walk from Chinatown to the Lower East Side — a former Jewish tenement district that’s become Manhattan’s nightlife capital — past the few remaining checked-tablecloth restaurants of Little Italy; past overflowing bars like Mehanata (known for its raucous live Balkan music); past heaps of trash, rats and neon signs; past elegant facades and newly built glass-walled apartment blocks I could never afford to live in, I felt a sense of home. Despite the price, despite the sheer brazen spirit, the bar had made my night (where else in the world would somebody charge $25 for a meticulously crafted piece of modern art that tastes exactly like seawater? And where else would you not mind all that much having to pay for it?).

Pan-fried dumplings at Nom Wah Tea Parlor. Image: Paul Wagtouicz

Gala night

That feeling of relentless, fervent optimism — that anything is possible — permeates the entirety of my time in New York. I feel it while I cycle down Fifth Avenue (New York’s Citi Bike bike-sharing scheme has recently expanded to cover most of Manhattan and Brooklyn), past the Metropolitan Museum of Art. Or when I head to the Hudson River on the West Side, where the waterfront has been transformed in recent years into a series of gorgeous gardens and modern-art installations.

One night, I check out the Fairytale Spring Ball ($50). Hosted by entertainment company Dances of Vice, the Brothers Grimm-themed extravaganza is set amid the colourful murals of Brooklyn’s Grand Prospect Hall: a 19th-century ballroom turned venue-for-hire. Revellers are outrageously costumed — someone has come as a swan queen, covered in feathers; someone else is Prince Charming in a Renaissance get-up; there are burlesque dancers, drag queens, live musicians and girls whose dresses turn into oversized fans, not to mention the occasional normally dressed couple on a would-be romantic date, looking utterly baffled.

On another occasion, I get discounted tickets (ordinarily, they start at $25 and go up to $300 or more) for the premiere performance of Strauss’s Der Rosenkavalier by the Metropolitan Opera at the Lincoln Center. Gala nights, I come to learn by watching my friend, photographer Rose Callahan, who runs the Last Night at the Met style blog for the opera house, are the best nights for people-watching. There are young men in jeans (ripped and unripped), girls in ball gowns and old women in floor-length white furs or impossibly elegant black silk. There are also men in perfectly cut tuxedos and girls in business casual.

It doesn’t matter to Rose whether the opera-goers dress up or dress down, she tells me; she’s on the hunt for people with a distinctive style all their own: people who look creative, rather than expensive.

As we all file out for the intermission and Rose sets up her camera, she stops — flabbergasted, and maybe a little bit terrified. Anna Wintour, the notoriously chilly editor-in-chief of Vogue, has just walked into shot. She barely raises an eyebrow, but she allows Rose to take the shot. “I think I accidentally walked into her companion,” Rose confides later.

Two days later, I’m at the other end of the city, walking with a friend in Crown Heights, a one-time Afro-Caribbean neighbourhood now known for its hipsterification. The Jamaican restaurant Glady’s, with its pulled-pork hash, fried plantains, and intensely sweet cocktails, is so crowded for brunch it’s almost impossible to get a table. It’s Sunday, and the storefront churches — Pentecostal, Assemblies of God — are filled with women, mostly black, mostly middle-aged, in their Sunday best: cream-coloured frock coats, floral hats, white canes. Through the windows of one, I can see women shouting and singing; through another, one is speaking in tongues. Halfway to Prospect Park, I’m stopped by a troop of preteen Girl Scouts, most in hijabs, who are selling the organisation’s famous branded cookies to raise money. They’re delighted, if a little surprised, to discover I’ve never had a Girl Scout cookie before.

“Try the Samoa!” one calls, defending her variety of choice, while another insists on the Thin Mint. They wait excitedly, and clap their hands when I at last pronounce them both delicious.

It’s this that’s the beauty of New York — no matter how much it changes. Different neighbourhoods may become trendy (before leaving Crown Heights, I noticed one of the local cafes had a dedicated ‘feminist lending library’); others may lose their cachet. The bars you love might close down, to be replaced by a speakeasy with a password you don’t yet know. You could meet a cab driver who’s secretly a millionaire, or pay $25 to run into the editor-in-chief of Vogue. You can walk through the Lower East Side at three in the morning to find yourself just one of many still outside, or make a left turn in Chinatown to find a cocktail bar you never knew existed. You can dress up like a swan queen and go to a Brooklyn ballroom to watch burlesque performers act out naughty fairytales, or you can eat Girl Scout cookies on a Sunday morning in Crown Heights while women in enormous hats stream out of storefront churches. You can spend $4 on an enormous plate of chicken feet, or $25 on a cocktail you can’t drink.

One minute, as Larry Kalkstein likes to say, you may be down, but the next — on a blossom-studded spring day in New York City — you’re up again.